A heartbreaking story is one that tugs at the heartstrings and brings on the tears. It's not an easy genre to write well though, for readers don't want to read loads of gush or tragedy that almost makes you laugh because it's so over-the-top. A good writer will put a lot of their own experience into a heartbreaking story, thereby connecting with it and making it seem a lot more real to the reader.

Steps

1

Reflect on the depth and breadth of the theme of your heartbreaking story. The theme can be broad or narrow, although the breadth will vary depending on whether you're writing a short story through to a novel. Plan out the basic story on paper, then backfill the heartbreaking moments, situations and themes that you want to introduce. This may help you to see how much the story will focus on a particular heartbreaking moment, or whether it will be a series of hardships leading to a pivotal disappointment or loss.

Do you want the story to have high points as well? Plan these in too, as juxtapositions to the less happy times being experienced by your characters. Or perhaps you don't want that––some characters might be on an ever-continuing downward spiral, whether of their own making or due to circumstances beyond their control.

2

Think through the specifics of the heartbreaking challenges facing your characters. There are many heartbreaking moments, situations and outcomes in life. As the author, your own idea of a heartbreaking moment will drive the reader's sense of it being sad, disappointing or shocking. However, here are some ideas of heartbreaking possibilities to focus on:

Loss of a loved one, a family member, a friend. Be it death, moving away, a rupture through an argument or disagreement, etc., this is top of the heartbreaking possibilities.

Broken romantic love is a good heartbreaking theme that never seems to tire the reader's interest (provided it's handled well, of course).

A series of unfortunate events happening to a good, caring character that just doesn't seem to get a break, such as losing a job, then their house, then failure in their start-up business, followed by a divorce, etc. It happens to people in real life and well-written, it can be heartbreaking as a series of events.

Loss of an animal or inability to save a habitat/piece or land/herd of animals, etc. can be a very heartbreaking theme. Many conservation, animal welfare and environmental themes are heartbreaking, including animals kept away from the wild behind cages, animals like elephants losing their own family members, etc.

Repetition of family behaviors that keep a family down on their luck through the decades/generations can make for a heartbreaking novel. Or, focus on a real family member you've researched who had a very hard life and a sad ending––this can have a real ring of truth because it's someone you really identify with.

Coping with a devastating illness, such as cancer, Alzheimer's, etc., can make for a heartbreaking story.

Homelessness, a descent into drug taking, selling/compromising ones dignity to survive, etc. are other possible themes.

3

Flesh out your characters. Name them, work out their motivations, character and loves. Get to know them so that they feel like real, living beings to you and you'll feel sorry for them or identify with them when the challenges begin facing them.

4

Write using your heart, not just your mind. In other words, allow your feelings to inform your writing. Realize some key things that you may experience when writing a heart-breaker:

You won't feel good. You may feel satisfaction with the manner in which you're crafting your work and writing but feelings-wise, provided you've created a good, substantial story with real characters, you'll identify with them and feel their pain and sorrows. On the plus side, this is a benefit because it will feed back into your descriptions and understanding of the character's progress.

Try to tell the story as you'd imagine your character seeing it, feeling it, experiencing it. However, in doing so, this can exhaust you mentally. You may actually cry––that's fine, you're really identifying with your character and their story. It's advised to take refreshing breaks though.

Avoid cynicism or cliched writing. Some writers of sad tales report blocking themselves off from the feelings, blending together the characters and feeling cynical about the whole genre. This can be a sign of writer's burnout or just focusing too much on the specifics without gaining broader perspective. Again, take breaks, even of a few days or weeks and come back to the story when you feel much refreshed.

5

Seek some balance. Life goes on regardless of the daily tragedies. This is what gives people hope that they too will return to normalcy some day. But it also gives contrast to your writing work, so that the reader can grasp the rhythm of everyday life continuing around the deep tragedy experienced by your character(s). This is like the background of an artist's canvas and needs to be a part of your tale to give it reality and depth.

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Tips

Don't worry too much about the title at this stage, unless it helps you stay on track. If your work does get published, the title is usually up for negotiation with your publisher anyway and they might see angles to a good title that you've missed. Of course, the exception to this is where you absolutely feel that the title is central to the book.

A good title for a story is never a title that literally states the plot.

Using and creating a central metaphor/quote that is repeated throughout the entire story can provide a good idea for a title, and also can make the reader even more attracted to the story.

The cigarette and the "Okay? Okay" quote from The Fault in Our Stars is a good example of this.

Making unrealistic things happen just for the sake of writing angst is unhelpful, and can be viewed as silly by the readers. For example, if an emotionally stable character's mother died last week, they will not jump off a bridge in sadness, especially if they have a loving family, and people who support them.

However, when dealing with mental instability, outrageous reactions can make things even sadder.

Warnings

Don't stress about it. If the story isn't unfolding, this is your mind's sign that you need to take a break and come back after your subconscious has digested more.